Driving Jobs in Winterset, IA — Now Hiring

As of May 2026, there are 50+ open driving positions in Winterset, IA. Current pay ranges from $14 to $151,200 per year. Top hiring areas include Delivery Driver, Cdl Driver and Warehouse. New roles are posted daily — listings on this page are verified and updated regularly.

United Parcel Service (UPS)

Winterset UPS Package Delivery Driver(Full-time)-United Parcel Service

Winterset, IA

$4,000 - $7,500

Clean Harbors

CDL B Vacuum Truck Driver-Industrial Cleaning|Winterset,IA|Clean

Winterset, IA

$23 - $31

Granite Construction

Winterset CDL B Water Truck Driver-Construction Site Dust Control with

Winterset, IA

$28 - $35

MTA New York City Transit

MTA New York City Transit Needs Transit Bus Driver-CDL B Public

Winterset, IA

$28 - $38

FedEx Ground

Winterset Full-time Opening:Delivery Driver-Package Handler | Hiring

Winterset, IA

$21 - $26

FedEx Custom Critical

Winterset Expedited Sprinter Van Driver-Time Critical Cargo

Winterset, IA

$84,000 - $151,200

DoorDash

Doordash(Winterset)Hiring:Morning Shift Delivery Driver | Apply Now

Winterset, IA

$2,970 - $5,060

Corporate Catering Couriers

$3.5k-$6k/Month Independent Contractor Driver-Catering Logistics job

Winterset, IA

$3,500 - $6,000

Foremost Transport

Urgent Hire in Winterset:Mobile Home Transport Driver-CDL A Oversize

Winterset, IA

$97,200 - $129,600

Uber Eats

Work in Winterset:Alcohol Delivery Driver | Hiring

Winterset, IA

$3,000 - $5,000

Heavy Freight Logistics

Winterset Independent Contractor Driver-Cargo Van / Box Truck

Winterset, IA

$5,000 - $8,500

XPO Logistics

Winterset Delivery Driver-Package Handler Box Truck with $22-$28/hr

Winterset, IA

$22 - $28

Driving Jobs in Winterset — FAQ

How many driving jobs are available in Winterset, IA right now?
There are currently 50+ open driving positions in Winterset, IA. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Winterset?
Driving job pay in Winterset varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Winterset?
Yes. Many delivery driver, courier, and DSP positions in Winterset require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Winterset?
Driving jobs in Winterset offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Winterset?
Benefits vary by employer, but many driving positions in Winterset offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Winterset?
Your take-home pay as a driver in Winterset depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Winterset?
Yes, many driving positions in Winterset are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 50+ listings above and apply directly.

Last updated: May 14, 2026